Milan Faces Challenges Ahead of Serie A Season

Tension grows in Milan. The calendar keeps moving; the squad does not.

With less than two weeks to go before the start of the 2026-27 Serie A season, Ruben Amorim is still waiting for two of the men who should be at the heart of his project. Mike Maignan and Adrien Rabiot, both central to France’s run deep into the 2026 World Cup, have decided to extend their holidays and will only report back to Milan a week before the league opener against Torino.

Amorim’s new era starts with absences

This was supposed to be the clean launch of a new cycle. New coach, new ideas, a pre-season to reset and rebuild. Instead, Amorim finds himself juggling an incomplete group and a transfer market that has yet to unlock.

Milan still need to move several first-team players out if they are to fund the reinforcements the Portuguese coach has requested. The Rafael Leao question hangs over everything: will the club’s most explosive talent still be in red and black when the window closes? No one inside Milanello can answer that with certainty yet.

Into that uncertainty drops another problem. Two of Amorim’s most senior figures are not on the training pitch.

Maignan and Rabiot were originally due back on August 14 after their World Cup exertions. The French pair have now pushed that date to August 16, exactly seven days before Milan kick off their campaign against Torino. For a new coach trying to install a demanding tactical framework, those 48 hours are not a minor detail.

Fans look across the city – and bristle

The reaction among some Rossoneri supporters has been sharp. They only have to glance across the city to find a comparison that stings.

Inter’s Lautaro Martinez and John Stones, also involved in the latter stages of the World Cup, are already back in full training under Cristian Chivu. While one half of Milan accelerates into the new season, the other feels stuck in neutral.

Rabiot’s position appears straightforward. During the World Cup he publicly underlined his intention to return, sit down with Amorim and “go again” in 2026-27. His delayed arrival frustrates, but it does not feel like a prelude to a rupture.

Maignan is a different story.

Maignan’s silence speaks loudly

On paper, he is the captain, the face of the dressing room, the man meant to embody the club’s competitive edge. In reality, every recent sign has pointed in the opposite direction.

The goalkeeper has stripped his social media accounts of photos and references to Milan, a gesture that in the modern game rarely comes without meaning. It has been interpreted by many around the club as a clear signal of discontent with life at San Siro.

Then came the moment that truly jarred. When Franco Baresi, one of the greatest figures in Milan’s history, was laid to rest last week, Maignan was not there. For a captain, the absence did not go unnoticed. Inside a club that lives on its legends, it raised more than just eyebrows.

Put together – the online scrub, the missed funeral, the extended holiday – a picture emerges of a relationship under strain, even if no official line has confirmed a break.

A delicate countdown

For Amorim, the clock is now his enemy. Every day without his captain and one of his most experienced midfielders is a day lost on the training ground: no time to refine pressing triggers, no time to drill build-up patterns, no time to test combinations before Torino arrive.

The new coach walked into Milan expecting a challenge. He has one. His tactical revolution will have to begin with a squad in flux, a market still open, and two key leaders only stepping back into the fold at the last possible moment.

Milan wanted a fresh start. Instead, they head into the final week before Serie A kicks off with questions hanging over their captain, their transfer plans, and the unity of a dressing room that has yet to fully report for duty.